1. Catalytic Hydrogenation of Alkenes Catalyst with Hydrogen adsorbed Catalyst with Hydrogen and alkene adsorbed Hydrogen inserted into C = C Alkane product released from catalyst Heterogeneous catalyst Pt. Pd. Ni-tinely divided metal SYN addition of hydrogen Alkene + H2 → Alkane

2. Heat evolved upon catalytic hydrogenation ( △ Ho) A MEASURE OF ALKENE STABILITY ALKENE C4H8 ALKANE C4H10 H2/Pd-C EXOTHERMIC Best to compare compounds that react to form same alkane Trans > Cis > Geminal ENERGY (-) 27.4 kcal/mol (-) 28.3 kcal/mol (-) 30.3 kcal/mol

3. SUMMARY OF ALKENE CHEMISTRY (illustrated with 1-methyl cyclopent-1-ene to emphasize transformation stereochemistry)

4. POLYOL NATURAL PRODUCTS ERYTHRONOLIDE A (ERYTHROMYCIN A) Antibiotic CELLULOSE Antifungal AMPHOTERICIN B

5. NATURAL PRODUCTS WITH ALKENE FUNCTIONALITY g-Bisabolene A sesquiterpene found in the essential oils of a number of plants Cembrene A diterpene from pine needles Limonene A monoterpene common in citrus fruits b-Carotene (A vitamin) A tetraterpene bright orange in color and the precursor to the visual pigment retinal Caryophyllene A constituent of clove oil Carvone Spearmint oil Vitamin A (vision)

6. MARKOVNIKOV and ANTI-MARKOVNIKOV ADDITION TO ALKENES In the dark, in the absence of peroxides polar solvents to promote formation of polar intermediate. Most substituted carbonium ion intermediate gives most substituted bromide product In the presence of peroxides and heat or light to promote homolytic cleavage of O-O bond. Most substituted radical intermediate gives least substituted bromide product Anti- Markovnikov

7. ALKENE POLYMERIZATION - SPECIAL TOPIC MONOMER STRUCTURE ethene propene Chloroethene (vinyl chloride) POLYMER (trade name) Polyethylene(polythene) Random co-polymer SARAN WRAP tetrafluoroethene acrylonitrile 1,1-dichloroethene and 1-chloroethene methylmethacrylate Phenylethene (styrene) Orlon(acrilan) TEFLON POLYSTYRNEN LUCITE(Plexiglass) polypropylene PVC(poly)vinyl chloride

8. FREE RADICAL POLYMERIZATION INITIATION, PROPAGATION (POLYMERIZATION) and TERMINATION STEPS TERMINATION POLYMERIZATION INITIATION

9. FREE RADICAL POLYMERIZATION INITIATION, PROPAGATION (POLYMERIZATION) and TERMINATION STEPS TERMINATION POLYMERIZATION INITIATION FREE RADICAL POLYMERIZATION INITIATION, PROPAGATION (POLYMERIZATION) and TERMINATION STEPS INITIATION POLYMERIZATION TERMINATION

10. CATIONIC POLYMERIZATION INITIATION, PROPAGATION (POLYMERIZATION) and TERMINATION STEPS INITIATION POLYMERIZATION TERMINATION Good monomer for cationic polymerization..Why? What about tetrafluoroethene?

11. CHOLESTEROL BIOSYNTHESIS Squalene Oxidosqualene cyclase Squalene epoxidase CHOLESTEROL

12. Oxidosqualene cyclase